[Hiring] Director of Product @Greenshades Software

Role Description

The Director of Product leads Greenshades' product organization — owning roadmap strategy, delivery execution, and product experience quality across our payroll, HR, and tax compliance solutions. This role carries a specific mandate to reorient product strategy for the AI era:

• Identifying where AI can reshape workflows, unlock new efficiencies, and differentiate the platform.
• Managing a team of Product Managers and a Product Experience/UX designer.
• Partnering closely with Engineering, Customer Experience, and Product Marketing to ensure the roadmap reflects real market and customer signal.
• Central to tightening the loop between what customers need and what gets built.

Responsibilities

• Lead, mentor, and develop a team of Product Managers and the Product Experience/UX function; set clear priorities, coach on craft, and manage performance and growth.
• Own and maintain a groomed, prioritized product roadmap that reflects the highest-value initiatives across Greenshades' product lines, grounded in customer and market signal.
• Drive Greenshades' product strategy into the AI era — evaluating where AI/ML can create step-change efficiency and experience improvements across the product line.
• Ensure roadmap prioritization reflects AI/ML integration rather than treating it as a bolt-on feature.
• Own Product Experience: ensure usability, design consistency, and overall product quality are considered alongside feature delivery.
• Drive day-to-day product delivery in close partnership with Engineering, ensuring features ship on time, within scope, and aligned with roadmap priorities.
• Partner with Customer Experience to strengthen how customer and market signal flows into intake, triage, and prioritization.
• Serve as a key product escalation point for significant customer and internal issues, working with Support, TPE, and Engineering to resolve or route issues appropriately.
• Partner with Product Marketing to ensure roadmap priorities, positioning, and launch timing are aligned and well-sequenced.
• Build and maintain deep working knowledge of payroll, HR, and tax business processes, including how AI is reshaping those domains.
• Partner with the CMO on Product team budget, resourcing, and prioritization tradeoffs; report on progress against roadmap and team capacity.
• Other duties as assigned.

Qualifications

• 5-7 years of product management experience in B2B SaaS or enterprise software, including 5+ years leading a team of Product Managers or equivalent ICs.
• Experience managing a complex domain (payroll, HR, tax, compliance, or similar), or a track record of quickly mastering a new business domain.
• Have shipped AI or ML-enabled capabilities in a B2B product, or led a roadmap shift toward AI.
• Experience hiring, coaching, and developing product talent, including managing performance and supporting career growth.
• Experience balancing roadmap strategy with hands-on delivery, including keeping features on schedule and in scope alongside Engineering.
• Experience working day to day with Engineering, Customer Success/CX, and Marketing to align product decisions with business priorities.
• Strong written and verbal communication, including explaining product strategy and tradeoffs to both technical and non-technical audiences.
• Experience presenting product strategy, roadmap progress, and resourcing tradeoffs to executive leadership.

Requirements

• Travel Required: Up to 15%
• Location: This is a remote position.